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Melt polycondensation of lactic acid

Ebru Tektemur1, Emine Bayraktar2, lk Mehmetolu3, Mehmet Saak4


1,2,3
Department of Chemical Engineering, Ankara University
4
Department of Chemistry, Ankara University
Address: 06100 Tandogan, Ankara/Turkey
Tel (+90312) 203 34 36; Fax: (+90312) 212 15 46.
1
ebrutektemur@eng.ankara.edu.tr; 2 bayrakta@eng.ankara.edu.tr, 3mehmet@eng.ankara.edu.tr
4
sacak@science.ankara.edu.tr
Plastics, that are cheaper and lighter than many materials, are being favored for
industrial and commercial applications. Plastics are necessary in daily life experience. We are
using them in household appliances, cars, packages ex. One of three of plastic raw materials
being used by package sector. The main environmental problem of conventional plastics are,
degrading in nature for centuries and produced by nonrenewal natural sources like petroleum,
coal and natural gas. Today, being recycling and environmentally friendly facilities come into
prominence for plastics.
In todays world of green chemistry and concern for the environment, PLA has
additional drivers that make it unique in the market place. The starting material for the final
polymer, lactic acid, can be made by a fermentation process using 100% annually renewable
resources. The polymer will also rapidly degrade in the environment and the by-products are
of very low toxicity, eventually being converted to carbon dioxide and water [1].
Lactic acid can be obtained from renewable sources like corn, potato, whey, sugar
cane through fermentation. Polylactic acid, PLA, is produced via polymerization of lactic acid
which is biocompatible and biodegradable polyester.
PLA can be produced by both direct condensation of lactic acid and by the ringopening polymerization (ROP) of the cyclic lactide dimer. The cost of producing PLA
using the ROP method is high due to the complicated purification process
of the lactide . Difficulty in driving the dehydration equilibrium to the direction of
esterification leads low molecular weight PLA when direct polycondensation method is used.
To avoid of the drawbacks, many investigators have suggested alternate synthesis routes such
as melt polycondensation and sequential melt/solid polycondensation [2].
In this study the effects of catalyst type on the molecular weight of polylactic acid was
investigated which was produced by melt polycondensation method. SnCl 2 (0.4 %wt / OLLA),
SnCl2 and TSA (p-toluen sulfonic acid) binary system(1:1 molar ratio), SnCl 2 and BA (boric
acid) binary system (1.5:1 molar ratio), Sb2O3 (0.5 %wt / OLLA) and Sn(Oct)2 (0.5
%wt/OLLA) is used as catalyst (Figure 1). BA and TSA are used as catalyst (Lewis acid,
SnCl2) activators. In all experiments oligomerization hold on first atm pressure, at 150C, for
2 hours then 150C, at 100 mmHg, for another 2 hour followed by 150C, at 30 mmHg, for 4
hour conditions. Polymerizations are done at 180C, at 10 mmHg, for 5 hours. Final product
is first dissolved in chloroform and precipitated in methanol. Then filtered and dried under
vacuum.

Figure 1. The effects of catalys type on the molecular weigh of PLA


Molecular weight of the resultant polymer analized with GPC. When SnCl2,
SnCl2/BA, SnCl2/TSA and Sb2O3 is used as catalyst, molecular weights are slightly different
from each other and approximately 26,000 Da. When Sn(Oct)2 is used as catalyst, the highest
molecular weight is achived.
References
1. David E. Henton, Patrick Gruber, Jim Lunt, and Jed Randall, Polylactic Acid Technology,
P:529, 2005
2. Lee,M., Tan, H., Chandrasekaran, M., Ooi, C., Synthesis and characterisation of PLLA by
melt polycondensastion using binary catalyst systems, SIMTech technical reports, Vol. 6,
P:40-44, 2005
Acknowledgments
The authors gratefully acknowledge the financial supports given to this work by Scientific
and Technical Research Council of Turkey, TUBITAK (Project No. 108M330).

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